Recently used a sizable portion of my refund in an effort to upgrade my audio set-up, and am currently looking to upgrade from the $30 Amp/DAC combo going on right now. From what I understand, there always comes a point where the price to gain ratio begins to steadily drop off, up until the point where you need to spend thousands of dollars to get any sort of improvement in your audio.

So my budget as of right now is $300, and I'm struggling as to what would be the best option available to me. I'm thinking of going with either a variation of the O2/ODAC combo (perhaps wait for the sleek Massdrop version to drop again?), or just settle for Schiit; from what I've heard the Schiit Stack is pretty great in regards to price/quality, though the Bifrost and Lyr version of said stack is one of the best on the market, even though it's expensive as hell.

If anyone could drop some advice on what I should get, please do so. If you can convince me of some other, cheaper, alternative, then all the better.